Darkwing tells a tale of an ancestor from 3 centuries ago named Darkwing Doubloon. The scene cuts to the royal family's ship with Seaman Drake handling the ship for the royal family a.k.a. the Muddlefoots. The ship is attacked by Negaduck and his pirate gang which includes Megavolt, Bushroot, Quackerjack and The Liquidator. They take the royal jewels and Negaduck tells them that he is a better pirate than the infamous Darkwing Doubloon. After the pirates have left, Drake tells the Muddlefoots that the ship is sinking and that he will go down with the ship while they get away on a lifeboat. It was all just a ruse so Drake could become Darkwing Doubloon and use the ship. He gets his crew, which includes Gosalyn, Launchpad, Gizmoduck, and Stegmutt. They set sail to find Negaduck and retrieve the jewels. They find them and board Negaduck's ship. As they are fighting, Gosalyn goes into Negaduck's quarters and takes the treasure and hands it out to the crew a little at the time and they sneak it back to their ship. Just as she hands the last of it to Stegmutt, she gets trapped in the chest and locked in. Darkwing acts as if he has been beaten and is thrown overboard. Back on the ship Darkwing realizes that Gosalyn is not there and knows that he must get her back. Gosalyn is discovered by Negaduck and he uses her as bait. Darkwing catches up to Negaduck and trades the treasure for Gosalyn who has secretly stolen Negaduck's map to his island. They are tricked and Negaduck sinks their ship and gets the treasure. Darkwing thinks that all is lost but Gosalyn tells him that he should not give up and they use Stegmutt for a boat and Gizmoduck provides propulsion and they use a map that Gosalyn stole to find Negaduck's island hideout. The Fearsome Pirates make it to the island and are bringing the treasure into his cave. They are ambushed one by one until Negaduck is the last one standing. He and Darkwing face off and Darkwing is triumphant in the end. Drake returns Negaduck's ship and the treasure to the royal family with The Fearsome Pirates as prisoners. Negaduck threatens Drake and Drake threatens to summon the Darkwing Doubloon. Negaduck's crew tells him to be quiet.
- With the door hinges on Negaduck's cabin on the inside, Launchpad should not have been able to open the door outwards when they were smuggling the jewels off Negaduck's ship. Stegmutt does the same thing when he leaves the cabin and then the door disappears for a second.
- When Launchpad is fighting Liquidator for the first time, Liquidator has an earring and then it disappears.
- When the royal family (the Muddlefoots) board the life raft, you can see the outline of Darkwing's face mask on Seaman Drake.
- As Darkwing Doubloon's ship reverses direction when Negaduck's ship attempts to crash into it, just as the ship jumps up from the water, you can hear a Goofy holler.
- Final appearance of Stegmutt.
- This is the only other Darkwing Duck episode besides "Tiff of the Titans" where Fenton (or, in this case, his ancestor) appears on this show outside his Gizmoduck suit.
- Due to this episode being set in a different time, this is the only episode not to feature Darkwing Duck himself.